WO2014071524A1 - Monomeric, oligomeric and polymeric semiconductors containing fused rings and their devices - Google Patents
Monomeric, oligomeric and polymeric semiconductors containing fused rings and their devices Download PDFInfo
- Publication number
- WO2014071524A1 WO2014071524A1 PCT/CA2013/050854 CA2013050854W WO2014071524A1 WO 2014071524 A1 WO2014071524 A1 WO 2014071524A1 CA 2013050854 W CA2013050854 W CA 2013050854W WO 2014071524 A1 WO2014071524 A1 WO 2014071524A1
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- WIPO (PCT)
- Prior art keywords
- substituted
- aryl
- alkyl
- alkenyl
- alkynyl
- Prior art date
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- OBCUTHMOOONNBS-UHFFFAOYSA-N phosphorus pentafluoride Chemical compound FP(F)(F)(F)F OBCUTHMOOONNBS-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- FPDOSPSUXAVNKK-UHFFFAOYSA-N selenopheno[3,2-b]thiophene Chemical compound [se]1C=CC2=C1C=CS2 FPDOSPSUXAVNKK-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- KXCAEQNNTZANTK-UHFFFAOYSA-N stannane Chemical group [SnH4] KXCAEQNNTZANTK-UHFFFAOYSA-N 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- APBDREXAUGXCCV-UHFFFAOYSA-L tetraethylazanium;carbonate Chemical compound [O-]C([O-])=O.CC[N+](CC)(CC)CC.CC[N+](CC)(CC)CC APBDREXAUGXCCV-UHFFFAOYSA-L 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- ONCNIMLKGZSAJT-UHFFFAOYSA-N thieno[3,2-b]furan Chemical compound S1C=CC2=C1C=CO2 ONCNIMLKGZSAJT-UHFFFAOYSA-N 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- GQHWSLKNULCZGI-UHFFFAOYSA-N trifluoromethoxybenzene Chemical compound FC(F)(F)OC1=CC=CC=C1 GQHWSLKNULCZGI-UHFFFAOYSA-N 0.000 description 1
- KKRPPVXJVZKJON-UHFFFAOYSA-N trimethyl-(5-trimethylstannylthiophen-2-yl)stannane Chemical compound C[Sn](C)(C)C1=CC=C([Sn](C)(C)C)S1 KKRPPVXJVZKJON-UHFFFAOYSA-N 0.000 description 1
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 1
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- H01G4/00—Fixed capacitors; Processes of their manufacture
- H01G4/002—Details
- H01G4/018—Dielectrics
- H01G4/06—Solid dielectrics
- H01G4/14—Organic dielectrics
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
- H01G9/004—Details
- H01G9/022—Electrolytes; Absorbents
- H01G9/025—Solid electrolytes
- H01G9/028—Organic semiconducting electrolytes, e.g. TCNQ
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/464—Lateral top-gate IGFETs comprising only a single gate
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/466—Lateral bottom-gate IGFETs comprising only a single gate
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Definitions
- Organic electronics can be manufactured at lower costs as compared to conventional silicon-based electronics and are suitable for widespread applications including displays, radio-frequency identification (RFID) tags, chemo-/biosensors, memory devices, solar cells, photodiodes, etc.
- organic semiconductors can be processed at low temperatures and deposited on plastic substrates to enable light weight, flexible, and ultra-thin electronic devices.
- organic semiconductors, especially solution-processed organic semiconductors have shown insufficient electronic performance as compared with inorganic semiconductors.
- the charge carrier mobility of solution-processed organic semiconductors is typically lower than 1 cm 2 V "1 s "1 , which is inadequate as channel semiconductor materials in organic thin film transistors (OTFTs) for many target applications. Therefore there is a need to develop solution-processable organic semiconductors, including monomers, oligomers and polymers, with mobility greater than 0.5 cm 2 V "1 s "1 .
- the present invention discloses semiconducting organic compounds comprising a fused-ring moiety, which can be used as high performance organic semiconductors for OTFTs, organic photovoltaics (OPVs), sensors, and other electronic devices.
- One objective of the present invention is to develop monomelic, oligomeric or polymeric semiconductor materials comprising said fused-ring moiety for electronic devices such as OTFTs, OPVs, and sensors. Another objective is to develop OTFTs, OPVs, sensors, and other electronic devices comprising said organic semiconductors comprising such fused-ring moieties.
- the present application also provides for a mixture or blend comprising one or more of said organic semiconducting compound and one or more compounds or polymers having semiconducting, charge transport, hole transport, electron transport, hole blocking, electron blocking, electrically conducting, photoconducting or light emitting properties. Further, the present application provides for a formulation comprising said organic semiconducting compound and an organic solvent.
- the present application provides for the use of said organic semiconducting compound as charge transport, semiconducting, electrically conducting, photoconducting or light emitting material in optical, electrooptical, electronic, electroluminescent or photoluminescent components or devices.
- present application provides for charge transport, semiconducting, electrically conducting, photoconducting or light emitting materials comprising said organic semiconducting compound.
- the present application also provides for a component or device comprising such organic semiconducting compound, said component or device being selected from the group consisting of organic field effect transistors (OFET), thin film transistors (TFT), integrated circuits (IC), logic circuits, capacitors, radio frequency identification (RFID) tags, devices or components, organic light emitting diodes (OLED), organic light emitting transistors (OLET), flat panel displays, backlights of displays, organic photovoltaic devices (OPV), organic solar cells (OSC), photodiodes, laser diodes, photoconductors, organic photodetectors (OPD), electrophotographic devices, electrophotographic recording devices, organic memory devices, sensor devices, charge injection layers, charge transport layers or interlay ers in polymer light emitting diodes (PLEDs), Schottky diodes, planarising layers, antistatic films, polymer electrolyte membranes (PEM), conducting substrates, conducting patterns, electrode materials in batteries, alignment layers, biosensors, biochips, security markings, security devices, and components
- the present application further relates to conjugated polymers comprising one or more repeating units which comprise said fused-ring moiety and/or one or more groups selected from aryl and heteroaryl groups.
- the invention further relates to monomers comprising said fused-ring moiety and further comprising one or more reactive groups which can be reacted to form a conjugated polymer as described herein.
- the invention also relates to small molecules comprising said fused-ring moiety and one or more inert groups.
- the invention further relates to the use of a polymer, formulation, mixture or polymer blend of the present invention as charge transport, semiconducting, electrically conducting, photoconducting or light emitting material, or in an optical, electrooptical, electronic, electroluminescent or photoluminescent device, or in a component of such a device or in an assembly comprising such a device or component.
- optical, electrooptical, electronic, electroluminescent and photoluminescent devices include, without limitation, organic field effect transistors (OFET), organic thin film transistors (OTFT), organic light emitting diodes (OLED), organic light emitting transistors (OLET), organic photovoltaic devices (OPV), organic photodetectors (OPD), organic solar cells, laser diodes, Schottky diodes, photoconductors and photodetectors.
- OFET organic field effect transistors
- OFT organic thin film transistors
- OLED organic light emitting diodes
- OLET organic light emitting transistors
- OLED organic light emitting transistors
- OLET organic light emitting transistors
- OLED organic light emitting transistors
- OLED organic light emitting transistors
- OLET organic photovoltaic devices
- OPD organic photodetectors
- organic solar cells laser diodes, Schottky diodes, photoconductors and photodetectors.
- the components of the above devices include, without limitation, charge injection layers, charge transport layers, interlayers, planarizing layers, antistatic films, polymer electrolyte membranes (PEM), conducting substrates and conducting patterns.
- charge injection layers charge transport layers
- interlayers interlayers
- planarizing layers antistatic films
- PEM polymer electrolyte membranes
- conducting substrates conducting patterns.
- the assemblies comprising such devices or components include, without limitation, integrated circuits (IC), radio frequency identification (RFID) tags or security markings or security devices containing them, flat panel displays or backlights thereof, electrophotographic devices, electrophotographic recording devices, organic memory devices, sensor devices, biosensors and biochips.
- IC integrated circuits
- RFID radio frequency identification
- Figure 1 depicts a typical bottom gate / top contact OTFT structure.
- Figure 2 depicts a typical bottom gate / bottom contact OTFT structure.
- Figure 3 depicts a typical top gate / bottom contact OTFT structure.
- Figure 4 depicts a typical top gate / top contact OTFT structure.
- Figure 5 shows the output (left) and transfer (right) characteristics of an OTFT device with PIBDFT-24 (annealed at 200 °C for 15 minutes) in the electron accumulation regime.
- L 30 ⁇
- W ⁇ mm.
- Figure 6 shows the output (left) and transfer (right) characteristics of an OTFT device with PIBDFV-24 (annealed at 200 °C for 15 minutes) in the electron accumulation regime.
- Figure 7 shows the output (left) and transfer (right) characteristics of an OTFT device with PIBDFV-26 (annealed at 200 °C for 15 minutes) in the electron accumulation regime.
- Figure 8 shows the output (left) and transfer (right) characteristics of an OTFT device with PIBDFV-40 (annealed at 200 °C for 15 minutes) in the electron accumulation regime.
- Figure 9 shows the output (left) and transfer (right) characteristics of an OTFT device with PIBDFBT-40 (annealed at 200 °C for 15 minutes) in the electron accumulation regime.
- L 30 ⁇
- W ⁇ mm.
- Figure 10 shows the output (left) and transfer (right) characteristics of an OTFT device with PIBDFBT-40 (annealed at 200 °C for 15 minutes) in the hole accumulation regime.
- L 30 ⁇
- W ⁇ mm.
- substituted is used to denote substitution, i.e. replacement of a hydrogen, by a substituent R s selected from the group consisting of halogen atoms, alkyl having from 1 to 60, preferably from 1 to 50, more preferably from 1 to 30 and most preferably from 1 to 20 carbon atoms, alkyl having from 1 to 60, preferably from 1 to 50, more preferably from 1 to 30 and most preferably from 1 to 20 carbon atoms wherein at least one of the hydrogen atoms is replaced by a halogen atom, alkyl having from 1 to 60, preferably from 1 to 50, more preferably from 1 to 30 and most preferably from 1 to 20 carbon atoms wherein at least one of the methylene moieties (C]3 ⁇ 4) is replaced by an oxygen atom, aryl having from 5 to 20 ring atoms with the ring atoms being independently of each other selected from the group consisting of carbon and heteroatoms as defined below, and ary
- polymer will be understood to mean a molecule of high relative molecular mass, the structure of which essentially comprises the multiple repetition of units derived, actually or conceptually, from molecules of low relative molecular mass (Pure Appl. Chem., 1996, 68, 2291).
- oligomer will be understood to mean a molecule of intermediate relative molecular mass, the structure of which essentially comprises a small plurality of units derived, actually or conceptually, from molecules of lower relative molecular mass (Pure Appl. Chem., 1996, 68, 2291).
- a polymer will be understood to mean a compound having > 1, i.e. at least 2 repeat units, preferably > 5 repeat units
- an oligomer will be understood to mean a compound with > 1 and ⁇ 10, preferably ⁇ 5, repeat units.
- polymer will be understood to mean a molecule that encompasses a backbone (also referred to as “main chain”) of one or more distinct types of repeat units (the smallest constitutional unit of the molecule) and is inclusive of the commonly known terms “oligomer”, “copolymer”, “homopolymer” and the like.
- polymer is inclusive of, in addition to the polymer itself, residues from initiators, catalysts and other elements attendant to the synthesis of such a polymer, where such residues are understood as not being covalently incorporated thereto. Further, such residues and other elements, while normally removed during post polymerization purification processes, are typically mixed or co-mingled with the polymer such that they generally remain with the polymer when it is transferred between vessels or between solvents or dispersion media.
- the terms “repeat unit”, “repeating unit” and “monomelic unit” are used interchangeably and will be understood to mean the constitutional repeating unit (CRU), which is the smallest constitutional unit the repetition of which constitutes a regular macromolecule, a regular oligomer molecule, a regular block or a regular chain (Pure Appl. Chem., 1996, 68, 2291).
- the term “unit” will be understood to mean a structural unit which can be a repeating unit on its own, or can together with other units form a constitutional repeating unit.
- a “terminal group” will be understood to mean a group that terminates a polymer backbone.
- terminal position in the backbone will be understood to mean a divalent unit or repeat unit that is linked at one side to such a terminal group and at the other side to another repeat unit.
- terminal groups include endcap groups or reactive groups that are attached to a monomer forming the polymer backbone which did not participate in the polymerisation reaction, like for example a group having the meaning of R e or R f as defined below.
- endcap group will be understood to mean a group that is attached to, or replacing, a terminal group of the polymer backbone.
- the endcap group can be introduced into the polymer by an endcapping process. Endcapping can be carried out for example by reacting the terminal groups of the polymer backbone with a monofunctional compound (“endcapper") like for example an alkyl- or arylhalide, an alkyl- or arylstannane or an alkyl- or arylboronate.
- endcapper can be added for example after the polymerisation reaction. Alternatively the endcapper can be added in situ to the reaction mixture before or during the polymerisation reaction.
- an endcapper can also be used to terminate the polymerisation reaction and thus control the molecular weight of the forming polymer.
- the terms "donor” or “donating” and “acceptor” or “accepting” will be understood to mean an electron donor and electron acceptor, respectively.
- Electrical donor will be understood to mean a chemical entity that donates electrons to another compound or another group of atoms of a compound.
- Electrical acceptor will be understood to mean a chemical entity that accepts electrons transferred to it from another compound or another group of atoms of a compound. See also International Union of Pure and Applied Chemistry, Compendium of Chemical Technology, Gold Book, Version 2.3.2, 19. August 2012, pages 477 and 480.
- n-type or n-type semiconductor will be understood to mean an extrinsic semiconductor in which the conduction electron density is in excess of the mobile hole density
- p-type or p-type semiconductor will be understood to mean an extrinsic semiconductor in which mobile hole density is in excess of the conduction electron density
- leaving group will be understood to mean an atom or group (which may be charged or uncharged) that becomes detached from an atom in what is considered to be the residual or main part of the molecule taking part in a specified reaction (see also Pure Appl. Chem., 1994, 66, 1134).
- conjugated will be understood to mean a compound (for example a polymer) that contains mainly C atoms with sp 2 -hybridisation (or optionally also sp-hybridization), and wherein these C atoms may also be replaced by hetero atoms. In the simplest case this is for example a compound with alternating C- C single and double (or triple) bonds, but is also inclusive of compounds with aromatic units like for example 1 ,4-phenylene.
- the term "mainly” in this connection will be understood to mean that a compound with naturally (spontaneously) occurring defects, or with defects included by design, which may lead to interruption of the conjugation, is still regarded as a conjugated compound. See also International Union of Pure and Applied Chemistry, Compendium of Chemical Technology, Gold Book, Version 2.3.2, 19. August 2012, pages 322-323.
- the molecular weight is given as the number average molecular weight M n or weight average molecular weight M w , which is determined by gel permeation chromatography (GPC) against polystyrene standards in eluent solvents such as tetrahydrofuran, trichloromethane (TCM, chloroform), chlorobenzene or 1,2,4-trichlorobenzene. Unless stated otherwise, 1,2,4- trichlorobenzene is used as solvent.
- GPC gel permeation chromatography
- TCM trichloromethane
- TCM trichloromethane
- 1,2,4- trichlorobenzene is used as solvent.
- the molecular weight distribution (“MWD”) which may also be referred to as polydispersity index (“PDI”), of a polymer is - Si delined as the ratio M w /M n .
- the degree of polymerization also referred to as total number of repeat units, m (or n)
- m (or n) M n /M u
- M n is the number average molecular weight
- M u is the molecular weight of the single repeat unit
- the present invention relates to the development and applications of monomeric, oligomeric and polymeric semiconductor materials comprising a fused-ring moiety (I):
- X is independently (i.e., the four X's in (I) can have different structures) oxygen (O), sulphur (S), or NR (R is independently hydrogen or optionally substituted hydrocarbon, cyclic and/or acyclic, with 1 to 60, in a first preferred aspect with 1 to 40 and in a second preferred aspect with 41 (or 45) to 60 carbon atoms such as, for example, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, and substituted aryl, or any other suitable group);
- M is a suitable conjugated moiety selected from, but not restricted to, the following structures and a combination of them:
- each structure can be substituted, where is applicable, with one or more suitable groups independently selected from optionally substituted hydrocarbon with about 1 to about 60, in a first preferred aspect with 1 to 40 and in a second preferred aspect with 41 (or 45) to 60 carbon (C) atoms (such as, for example, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, alkoxy, and substituted alkoxy), cyano (CN), nitro, and halogen, or any other suitable group.
- suitable groups independently selected from optionally substituted hydrocarbon with about 1 to about 60, in a first preferred aspect with 1 to 40 and in a second preferred aspect with 41 (or 45) to 60 carbon (C) atoms (such as, for example, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl,
- alkyl or alkoxy radical i.e. where the terminal C3 ⁇ 4 group is replaced by -0-, can be straight-chain or branched.
- Suitable examples of such alkyl and alkoxy radical are methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy, octoxy, nonoxy, decoxy, undecoxy, dodecoxy, tridecoxy or tetradecoxy.
- Preferred alkyl and alkoxy radicals have from 1 to 60, preferably from 1 to 50, more preferably from 1 to 40, even more preferably from 1 to 30 and most preferably from 1 to 20 carbon atoms.
- Suitable examples of such preferred alkyl and alkoxy radicals may be selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, 2-ethylhexyl, 2- butyloctyl, 2-hexyldecyl, 2-octyldodecyl, 2-decyltetradecyl, 4-decylhexadecyl, 7- decylnonadecyl, 4-octadecyldocosyl, methoxy, ethoxy, propoxy, butoxy, pentoxy,
- alkenyl groups may be selected from the group consisting of vinyl, prop-l-enyl, or prop-2-enyl, but-l-enyl, but-2-enyl or but-3-enyl, pent-l-enyl, pent-2-enyl, pent-3- enyl or pent-4-enyl, hex-l-enyl, hex-2-enyl, hex-3-enyl, hex-4-enyl or hex-5-enyl, hept-l-enyl, hept-2-enyl, hept-3-enyl, hept-4-enyl, hept-5-enyl or hept-6-enyl, oct-l-enyl, oct-2-enyl, oct-3-enyl, oct-4-enyl, oct-5-enyl, oct-6-enyl or oct
- alkenyl groups are C2-C2o-lE-alkenyl, C4-C2o-3E-alkenyl, C5-C 2 o-4-alkenyl, and C6-C2 0 -5 -alkenyl, in particular C2-C7-lE-alkenyl, C4-C7-3E- alkenyl and Cs-C7-4-alkenyl.
- alkenyl groups examples are vinyl, lE-propenyl, lE-butenyl, lE-pentenyl, lE-hexenyl, lE-heptenyl, 3-butenyl, 3E-pentenyl, 3E-hexenyl, 3E-heptenyl, 4-pentenyl, 4Z-hexenyl, 4E-hexenyl, 4Z-heptenyl, 5-hexenyl, 6-heptenyl and the like.
- Alkenyl groups having up to 12 C atoms are generally preferred.
- Very preferred substituents L are selected from halogen, most preferably F, or alkyl, alkoxy, oxaalkyl, thioalkyl, fluoroalkyl and fluoroalkoxy with 1 to 24 or with 1 to 12 C atoms or alkenyl, and alkynyl with 2 to 24 or with 2 to 12 C atoms.
- aryl and heteroaryl groups are phenyl, phenyl whereinone or more CH groups are replaced by N, naphthalene, thiophene, selenophene, thienothiophene, dithienothiophene, fluorene and oxazole, all of which can be unsubstituted, mono- or polysubstituted with L as defined above.
- Very preferred rings are selected from pyrrole, preferably N-pyrrole, furan, pyridine, preferably 2- or 3- pyridine, pyrimidine, pyridazine, pyrazine, triazole, tetrazole, pyrazole, imidazole, isothiazole, thiazole, thiadiazole, isoxazole, oxazole, oxadiazole, thiophene, preferably 2-thiophene, selenophene, preferably 2-selenophene, thieno[3,2- b]thiophene, thieno[2,3-b]thiophene, furo[3,2-b]furan, furo[2,3-b]furan, seleno[3,2- b] selenophene, seleno[2,3-b]selenophene, thieno[3,2-b]furan, thieno[3,2-b]selenophene
- (I) is one of the following exemplary structures:
- R is independently hydrogen or optionally substituted hydrocarbon with 1 to 60, in a first preferred aspect with 1 to 40 and in a second preferred aspect with 41 (or 45) to 60 carbon atoms such as, for example, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, and substituted aryl, or any other suitable group;
- R' is independently hydrogen or optionally substituted hydrocarbon with 1 to 60, in a first preferred aspect with 1 to 40 and in a second preferred aspect with 41 (or 45) to 60 carbon atoms such as, for example, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, and substituted aryl, or any other suitable group; each structure can be further substituted, where is applicable, with one or more suitable groups independently selected from optionally substituted hydrocarbon with 1 to 60, in a first preferred aspect with 1 to 40 and in a second preferred aspect with 41 (or 45) to 60 carbon atoms (such as, for example, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, alkoxy, and substituted alkoxy), cyano (CN), nitro, and halogen, or any other suitable group.
- CN
- (I) is one of the following structures
- R is independently hydrogen or optionally substituted hydrocarbon with 1 to 60, in a first preferred aspect with 1 to 40 and in a second preferred aspect with 41 (or 45) to 60 carbon atoms such as, for example, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, and substituted aryl, or any other suitable group;
- each structure can be further substituted, where is applicable, with one or more suitable groups independently selected from optionally substituted hydrocarbon with 1 to 60, in a first preferred aspect with 1 to 40 and in a second preferred aspect with 41 (or 45) to 60 carbon atoms (such as, for example, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, alkoxy, and substituted alkoxy), cyano (CN), nitro, and halogen, or any other suitable group;
- suitable groups independently selected from optionally substituted hydrocarbon with 1 to 60, in a first preferred aspect with 1 to 40 and in a second preferred aspect with 41 (or 45) to 60 carbon atoms (such as, for example, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, alkoxy, and substituted alk
- this invention relates to the development of monomeric, oligomeric and polymeric semiconductor materials comprising a moiety (I) with the following general structure (PI) and (PII):
- a is an integer from 1 to 20;
- b or c is an integer from 0 (zero) to 20;
- the unit Ar and the unit Mi-(I)-M 2 can be connected in a random or alternating manner, e.g., (PI) or (PII) can be a random copolymer, an alternating copolymer, or a block copolymer;
- n is a number from about 1 to 1,000,000;
- the terminal "*" can be hydrogen or any other suitable group or moiety.
- Ar is independently (i.e. in the case of b>l, each Ar may have a different structure from the other) a ⁇ -conjugated moiety selected from, but not restricted to, the following structures and a combination of them:
- each structure can be substituted, where is applicable, with one or more suitable groups independently selected from optionally substituted hydrocarbon with 1 to 60, in a first preferred aspect with 1 to 40 and in a second preferred aspect with 41 (or 45) to 60 carbon atoms (such as, for example, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, alkoxy, and substituted alkoxy), cyano (CN), nitro, and halogen, or any other suitable group;
- R is independently hydrogen, optionally substituted hydrocarbon with 1 to 60, in a first preferred aspect with 1 to 40 and in a second preferred aspect with 41 (or 45) to 60 carbon atoms (such as, for example, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, or substituted aryl), or any other suitable group;
- Mi and M2 are independently a ⁇ -conjugated moiety selected from, but not restricted to, the following structures and a combination of them
- each structure can be substituted, where is applicable, with one or more suitable groups independently selected from optionally substituted hydrocarbon with 1 to 60, in a first preferred aspect with 1 to 40 and in a second preferred aspect with 41 (or 45) to 60 carbon atoms (such as, for example, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, alkoxy, and substituted alkoxy), cyano (CN), nitro, and halogen, or any other suitable group;
- R is independently hydrogen, optionally substituted hydrocarbon with 1 to 60, in a first preferred aspect with 1 to 40 and in a second preferred aspect with 41 (or 45) to 60 carbon atoms (such as, for example, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, or substituted aryl), or any other suitable group.
- (PI) and (PII) are selected form the following structures:
- Mi, M 2 , Ar, R, a, b, and n are defined as above; each structure can be substituted, where is applicable, with one or more suitable groups independently selected from optionally substituted hydrocarbon with 1 to 60, in a first preferred aspect with 1 to 40 and in a second preferred aspect with 41 (or 45) to 60 carbon atoms (such as, for example, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, alkoxy, and substituted alkoxy), cyano (CN), nitro, and halogen, or any other suitable group;
- suitable groups independently selected from optionally substituted hydrocarbon with 1 to 60, in a first preferred aspect with 1 to 40 and in a second preferred aspect with 41 (or 45) to 60 carbon atoms (such as, for example, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alky
- n is a number from 1 to 1,000,000
- ⁇ ⁇ ⁇ indicates the linkage can be a cis- or trans-structure
- the terminal "*" can be hydrogen or any other suitable group or moiety.
- R is independently selected from hydrogen, optionally substituted hydrocarbon with 1 to 60, in a first preferred aspect with 1 to 40 and in a second preferred aspect with 41 (or 45) to 60 carbon atoms (such as, for example, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, and substituted aryl), or any other suitable group;
- each structure can be substituted, where is applicable, with one or more suitable groups independently selected from optionally substituted hydrocarbon with 1 to 60, in a first preferred aspect with 1 to 40 and in a second preferred aspect with 41 (or 45) to 60 carbon atoms (such as, for example, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, alkoxy, and substituted alkoxy), cyano (CN), nitro, and halogen, or any other suitable group;
- suitable groups independently selected from optionally substituted hydrocarbon with 1 to 60, in a first preferred aspect with 1 to 40 and in a second preferred aspect with 41 (or 45) to 60 carbon atoms (such as, for example, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, alkoxy, and substituted alkoxy
- n is a number from 1 to 1,000,000
- terminal “*” can be hydrogen or any other suitable group or moiety.
- Other groups or moieties suitable as "*" may be as defined for R a or R° below.
- Compounds comprising said fused-ring moiety as defined above may preferably be selected from the group consisting of small molecules, monomers and polymers.
- small molecule will be used to denote a compound comprising said fused-ring moiety and two inert chemical groups, which are inert under use condition and thus inhibit such a small molecule from being polymerized.
- monomer is used to denote a compound comprising said fused-ring moiety and at least one reactive chemical group, which allows such monomer to be reacted so as to form part of a polymer.
- EA-1 A monomer, oligomer or polymer comprising a fused-ring moiety (I):
- X is independently oxygen (O), sulphur (S), or NR (R is independently hydrogen or optionally substituted hydrocarbon with 1 to 40 carbon atoms such as, for example, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, and substituted aryl, or any other suitable group);
- M is a conjugated moiety
- EA-2 The monomer, oligomer or polymer of EA-1, wherein M is selected from a group of structures:
- each structure can be substituted, where is applicable, with one or more suitable groups independently selected from optionally substituted hydrocarbon with about 1 to about 40 carbon atoms (such as, for example, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, alkoxy, and substituted alkoxy), cyano (CN), nitro, and halogen, or any other suitable group.
- suitable groups independently selected from optionally substituted hydrocarbon with about 1 to about 40 carbon atoms (such as, for example, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, alkoxy, and substituted alkoxy), cyano (CN), nitro, and halogen, or any other suitable group.
- EA-3 The monomer, oligomer or polymer of EA-1, wherein (I) is selected from the following structures:
- R is independently hydrogen or optionally substituted hydrocarbon with 1 to 40 carbon atoms such as, for example, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, and substituted aryl, or any other suitable group;
- R' is independently hydrogen or optionally substituted hydrocarbon with 1 to 40 carbon atoms such as, for example, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, and substituted aryl, or any other suitable group;
- each structure can be further substituted, where is applicable, with one or more suitable groups independently selected from optionally substituted hydrocarbon with 1 to 40 carbon atoms (such as, for example, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, alkoxy, and substituted alkoxy), cyano (CN), nitro, and halogen, or any other suitable group.
- EA-4 A monomer, oligomer or polymer of EA-1 to EA-3 with the following structure PI and PII:
- PI PII
- X, M and R are defined as above; a is an integer from 1 to 20; b or c is an integer from 0 (zero) to 20; the unit Ar and the unit Mi-(I)-M 2 can be connected in a random or alternating manner, i.e., (PI) or (PII) can be a random copolymer, an alternating copolymer, or a block copolymer; n is a number from 1 to 1,000,000; indicates the linkage can be a cis- or trans-structure; the terminal "*" can be hydrogen or any other suitable group or moiety; Ar is independently a ⁇ -conjugated moiety.
- EA-5 The monomer, oligomer or polymer of EA-4, wherein Ar is independently selected from the following structures or a combination of the following structures:
- R is independently hydrogen or optionally hydrocarbon of alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, or substituted aryl with 1 to 40 carbon atoms;
- each structure can be substituted, where is applicable, with one or more suitable groups independently selected from optionally substituted hydrocarbon with 1 to 40 carbon atoms (such as, for example, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, alkoxy, and substituted alkoxy), cyano (CN), nitro, and halogen, or any other suitable group.
- EA-6 The monomer, oligomer or polymer of EA-4 and EA-5, wherein Ar are optionally substituted with one or more suitable groups independently selected from optionally substituted hydrocarbon with 1 to 40 carbon atoms, nitro, and halogen.
- EA-7 The monomer, oligomer or polymer of EA-4, which has one of the following structures.
- Mi, M 2 , Ar, R, a, b, and n are defined as above;
- each structure can be substituted, where is applicable, with one or more suitable groups independently selected from optionally substituted hydrocarbon with 1 to 40 carbon atoms (such as, for example, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, alkoxy, and substituted alkoxy), cyano (CN), nitro, and halogen, or any other suitable group;
- suitable groups independently selected from optionally substituted hydrocarbon with 1 to 40 carbon atoms (such as, for example, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, alkoxy, and substituted alkoxy), cyano (CN), nitro, and halogen, or any other suitable group;
- n is a number from 1 to 1,000,000
- ⁇ ⁇ ⁇ indicates the linkage can be a cis- or trans-structure
- the terminal "*" can be hydrogen or any other suitable group or moiety.
- EA-8 The monomer, oligomer or polymer EA-4 and EA-7 is selected from above structures (1) through (230) wherein:
- R is independently selected from hydrogen, optionally substituted hydrocarbon with 1 to 40 carbon atoms (such as, for example, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, and substituted aryl), or any other suitable group;
- each structure can be substituted, where is applicable, with one or more suitable groups independently selected from optionally substituted hydrocarbon with 1 to 40 carbon atoms (such as, for example, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, alkoxy, and substituted alkoxy), cyano (CN), nitro, and halogen, or any other suitable group;
- suitable groups independently selected from optionally substituted hydrocarbon with 1 to 40 carbon atoms (such as, for example, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, alkoxy, and substituted alkoxy), cyano (CN), nitro, and halogen, or any other suitable group;
- n is a number from 1 to 1,000,000
- the terminal "*" can be hydrogen or any other suitable group or moiety.
- the present application relates to the following aspects EB-1 to EB-8: EB-1.
- X is independently oxygen (O), sulphur (S), or NR (R is independently hydrogen or optionally substituted hydrocarbon with 41 (or 45) to 60 carbon atoms such as, for example, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, and substituted aryl, or any other suitable group);
- M is a conjugated moiety
- EB-2 The monomer, oligomer or polymer of EB-1, wherein M is selected from a group of structures:
- each structure can be substituted, where is applicable, with one or more suitable groups independently selected from optionally substituted hydrocarbon with about 41 (or 45) to about 60 carbon atoms (such as, for example, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, alkoxy, and substituted alkoxy), cyano (CN), nitro, and halogen, or any other suitable group.
- suitable groups independently selected from optionally substituted hydrocarbon with about 41 (or 45) to about 60 carbon atoms (such as, for example, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, alkoxy, and substituted alkoxy), cyano (CN), nitro, and halogen, or any other suitable group.
- R is independently hydrogen or optionally substituted hydrocarbon with 41 (or 45) to 60 carbon atoms such as, for example, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, and substituted aryl, or any other suitable group;
- R' is independently hydrogen or optionally substituted hydrocarbon with 41 (or 45) to 60 carbon atoms such as, for example, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, and substituted aryl, or any other suitable group;
- each structure can be further substituted, where is applicable, with one or more suitable groups independently selected from optionally substituted hydrocarbon with 41 (or 45) to 60 carbon atoms (such as, for example, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, alkoxy, and substituted alkoxy), cyano (CN), nitro, and halogen, or any other suitable group.
- EB-4 A monomer, oligomer or polymer of EB-1 to EB-3 with the following structure PI and PII:
- PI PII
- X, M and R are defined as above; a is an integer from 1 to 20; b or c is an integer from 0 (zero) to 20; the unit Ar and the unit Mi-(I)-M 2 can be connected in a random or alternating manner, i.e., (PI) or (PII) can be a random copolymer, an alternating copolymer, or a block copolymer; n is a number from 1 to 1,000,000; indicates the linkage can be a cis- or trans-structure; the terminal "*" can be hydrogen or any other suitable group or moiety; Ar is independently a ⁇ -conjugated moiety.
- EB-5 The monomer, oligomer or polymer of EB-4, wherein Ar is independently selected from the following structures or a combination of the following structures:
- R is independently hydrogen or optionally hydrocarbon of alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, or substituted aryl with 41 (or 45) to 60 carbon atoms;
- each structure can be substituted, where is applicable, with one or more suitable groups independently selected from optionally substituted hydrocarbon with 41 (or 45) to 60 carbon atoms (such as, for example, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, alkoxy, and substituted alkoxy), cyano (CN), nitro, and halogen, or any other suitable group.
- EB-6 The monomer, oligomer or polymer of EB-4 and EB-5, wherein Ar are optionally substituted with one or more suitable groups independently selected from optionally substituted hydrocarbon with 41 (or 45) to 60 carbon atoms, nitro, and halogen.
- EB-7 The monomer, oligomer or polymer of EB-4, which has one of the following structures.
- each structure can be substituted, where is applicable, with one or more suitable groups independently selected from optionally substituted hydrocarbon with 41 (or 45) to 60 carbon atoms (such as, for example, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, alkoxy, and substituted alkoxy), cyano (CN), nitro, and halogen, or any other suitable group; n is a number from 1 to 1,000,000;
- ⁇ ⁇ ⁇ indicates the linkage can be a cis- or trans-structure
- the terminal "*" can be hydrogen or any other suitable group or moiety.
- EB-8 The monomer, oligomer or polymer EB-4 and EB-7 is selected from above structures (1) through (230) wherein:
- R is independently selected from hydrogen, optionally substituted hydrocarbon with 41 (or 45) to 60 carbon atoms (such as, for example, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, and substituted aryl), or any other suitable group;
- each structure can be substituted, where is applicable, with one or more suitable groups independently selected from optionally substituted hydrocarbon with 41 (or 45) to 60 carbon atoms (such as, for example, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, alkoxy, and substituted alkoxy), cyano (CN), nitro, and halogen, or any other suitable group; n is a number from 1 to 1,000,000;
- the terminal "*" can be hydrogen or any other suitable group or moiety.
- Monomers containing (I) can be readily synthesized by known procedures in the literature such as, for example, Connor, et al. U. S. Patent 6492533 Bl (Dec. 10, 2002) and esvadba, et al. U. S. Patent 6503937 Bl.
- the monomeric, oligomeric or polymeric materials comprising moiety (I) in the present invention can be used in electronic devices such as thin film transistors, photovoltaics, and sensors.
- the use of the present monomer, oligomer or polymer as a semiconductor in electronic devices is illustrated herein using thin film transistors.
- Figure 1 there is schematically illustrated a bottom- gate, top-contact OTFT configuration comprised of a substrate, in contact therewith a gate electrode and a layer of a gate dielectric. On top of the gate dielectric there is an organic semiconductor layer. Two conductive contacts, source electrode and drain electrode, are deposited on top of the organic semiconductor layer.
- Figure 2 schematically illustrates a bottom-gate, bottom-contact OTFT configuration comprised of a substrate, a gate electrode, a source electrode and a drain electrode, a gate dielectric layer, and an organic semiconductor layer.
- Figure 3 schematically illustrates a top-gate, bottom-contact OTFT configuration comprised of a substrate, a gate electrode, a source electrode and a drain electrode, a gate dielectric layer, and an organic semiconductor layer.
- Figure 4 schematically illustrates a top-gate, top-contact OTFT configuration comprised of a substrate, a gate electrode, a source electrode and a drain electrode, a gate dielectric layer, and an organic semiconductor layer.
- Figure 5 shows the output (left) and transfer (right) characteristics of an OTFT device with PIBDFT-24 (annealed at 200 °C for 15 minutes) in the electron accumulation regime.
- L 30 ⁇
- W ⁇ mm.
- Figure 6 shows the output (left) and transfer (right) characteristics of an OTFT device with PIBDFV-24 (annealed at 200 °C for 15 minutes) in the electron accumulation regime.
- Figure 7 shows the output (left) and transfer (right) characteristics of an OTFT device with PIBDFV-26 (annealed at 200 °C for 15 minutes) in the electron accumulation regime.
- Figure 8 shows the output (left) and transfer (right) characteristics of an OTFT device with PIBDFV-40 (annealed at 200 °C for 15 minutes) in the electron accumulation regime.
- Figure 9 shows the output (left) and transfer (right) characteristics of an OTFT device with PIBDFBT-40 (annealed at 200 °C for 15 minutes) in the electron accumulation regime.
- Figure 10 shows the output (left) and transfer (right) characteristics of an OTFT device with PIBDFBT-40 (annealed at 200 °C for 15 minutes) in the hole accumulation regime.
- the semiconductor layer has a thickness ranging for example from about 10 nanometers to about 1 micrometer with a preferred thickness of from about 20 to about 200 nanometers.
- the OTFT devices contain a semiconductor channel with a width, W and length, L,
- the semiconductor channel width may be, for example, from about 1 micrometer to about 5 millimeters, with a specific channel width being about 5 micrometers to about 1 millimeter.
- the semiconductor channel length may be, for example, from about 10 nanometers to about 1 millimeter with a more specific channel length being from about 20 nanometers to about 500 micrometers.
- the present application provides for a small molecule, i.e. for a compound comprising said fused-ring moiety and two inert chemical groups R a and R b .
- a small molecule may for example be represented by formula (Il-a)
- Such inert chemical groups R a and R b may independently of each other for example be chosen from the group consisting of hydrogen, fluorine, alkyl having from 1 to 60, preferably from 1 to 50, more preferably from 1 to 30 and most preferably from 1 to 20 carbon atoms, fluoroalkyl having from 1 to 60, preferably from 1 to 50, more preferably from 1 to 30 and most preferably from 1 to 20 carbon atoms, aromatic ring systems of from 5 to 30 carbon atoms and aromatic ring systems of from 5 to 30 carbon atoms wherein one or more hydrogen atom may independently of each other be replaced by fluorine or alkyl having from 1 to 40, preferably from 1 to 30, more preferably from 1 to 20 and most preferably from 1 to 10 carbon atoms.
- R° reactive chemical group
- such a monomer may comprise two reactive chemical groups and is for example represented by formula (Il-b) R°-Q-R d (Il-b) wherein Q comprises said fused-ring moiety and R° and R d are reactive chemical groups as defined above for R°.
- Q in formulae (Il-a) and (Il-b) may further comprise one or more (for example 2, 3, 4, 5, 6, 7, 8, 9 or 10) aryl or heteroaryl as defined above.
- Preferred examples of Q may be comprise, preferably consist of, the following
- Ar a , Ar b and Ar° are independently of each other aryl or heteroaryl different from U a and U b ; ml, m2, m3 and m4 are independently of each other selected from the group consisting of 0, 1 and 2, with the provision that at least one of ml and m3 is not 0; and m5 is 0 or an integer from 1 to 10 (for example 2, 3, 4, 5, 6, 7, 8 or 9).
- Ar a , Ar b and Ar° are selected from aryl having from 5 to 30 ring atoms and heteroaryl having from 5 to 30 ring atoms.
- Said aryl and heteroaryl may optionally be substituted with at least one substituent L as defined earlier.
- Preferred substituents L are selected from alkyl having from 1 to 60 carbon atoms, more preferably from alkyl having from 1 to 40 carbon atoms, even more preferably from alkyl having from 1 to 30 carbon atoms and most preferably from alkyl having from 1 to 20 carbon atoms.
- said alkyl may be partially or completely fluorinated.
- Preferred small molecules and monomers are those with Q selected from one of the following formula (III-a-1) and (III-a-2)
- Q of formulae (III), (III-a-1), (III-a-2) and (III-b-1) to (III-b-5) are those wherein one or more of Ar a , Ar b and Ar° denote aryl or heteroaryl, preferably having electron donor properties or electron acceptor properties.
- Suitable examples of aryl and heteroaryl with electron donor properties may be selected from the group consisting of the following formulae (Dl) to (D126)
- R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 and R 18 being independently of each other selected from the group consisting of hydrogen, F, Br, CI, -CN, -NC, -NCO, -NCS, -OCN, -SCN, -C(0)NR°R°°, -C(0)X°, - C(0)R°, -NH 2 , -NR°R 00 , -SH, -SR°, -S0 3 H, -S0 2 R°, -OH, -N0 2 , -CF 3 , -SF 5 , optionally substituted silyl or hydrocarbyl with 1 to 60, preferably with 1 to 50 and more preferably with 1 to 40 C atoms that is optionally substituted and optionally comprises one or more hetero atoms, with X°, R° and R 00 as defined earlier.
- Suitable examples of aryl and heteroaryl with electron acceptor properties may be selected from the group consisting of the following formula (A-l) to (A-91)
- POLYMER in a further aspect provides for an oligomer or polymer, i.e. for a compound comprising more than one said fused-ring moiety.
- oligomer or polymer comprises more than one group Q as defined in any one of formulae (III), (III-a-1), (III-a-2) and (III-b-1) to (III-b-5).
- Q may be the same or different.
- such oligomer or polymer may further comprise a repeating unit comprising a group selected from monocyclic or polycyclic aryl or heteroaryl groups that are optionally substituted.
- a repeating unit comprising a group selected from monocyclic or polycyclic aryl or heteroaryl groups that are optionally substituted.
- such further repeating units are selected from one of the following
- Ar a , Ar b , Ar°, m2, m4 and m5 are as defined above;
- Ar d and Ar e are independently of each aryl or heteroaryl with electron donor properties or electron acceptor properties, preferably independently of each other chosen from the group consisting of formulae (D-l) to (D-126) and (A-l) to (A-91); and
- n6 and m7 are independently of each other 0, 1 or 2, provided that at least one of m6 and m7 is not 0 (for example m6 is 0 and m7 is 1, or m6 is 1 and m7 is 0, or m6 is 1 and m7 is 1).
- Preferred oligomers and polymers may for example comprise a polymer chain of formula (V) wherein
- n is an integer > 1 ;
- Q 1 , Q 2 and Q 3 are independently of each other monomeric units as defined below, provided that at least one of Q 1 , Q 2 and Q 3 comprises said fused- ring moiety;
- mx is > 0 and ⁇ 1 ;
- Q 1 , Q 2 and Q 3 are independently of each other selected from the group consisting of Q as defined in and for above formulae (III), (III-a-1), (III-a-2) and (III- b-l) to (III-b-5).
- Examples of suitable polymer chains of formula (IV) may be selected from the following formulae (V-l) to (V-10)
- Such polymers can be alternating or random copolymers.
- the total number m of repeating units is preferably from 2 to 10000.
- the total number m of repeating units is preferably at least 10 and most preferably at least 50.
- the present oligomers and polymers include homopolymers and copolymers, such as for example statistical or random copolymers, alternating copolymers and block copolymers as well as any combination of these.
- polymers selected from the following groups
- Group 1 consisting of homopolymers of the unit U a or (Ar a -U a ) or (Ar a -U a -Ar b ) or (Ar a -U a -Ar c ) or (U a -Ar b -Ar c ) or (Ar a -U a -Ar b -Ar c ) or (U a -Ar a -U a ), i.e. where all repeating units are identical,
- Group 2 consisting of random or alternating copolymers formed by identical units (Ar a -U a -Ar b ) or (U a -Ar a -U a ) and identical units (Ar c ),
- Group 3 consisting of random or alternating copolymers formed by identical units (Ar a -U a -Ar b ) or (U a -Ar a -U b ) and identical units (Ar a ),
- Group 4 consisting of random or alternating copolymers formed by identical units (Ar a -U a -Ar b ) or (U a -Ar a -U b ) and identical units (Ar a -Ar d -Ar b ) or (Ar d -Ar a - Ar e ),
- Ar a , Ar b , Ar c , Ar d , Ar e , U a and U b are as defined above and below, in groups 1, 2 and 3 Ar a , Ar b and Ar c are different from a single bond, and in group 4 one of Ar a and Ar b may also denote a single bond .
- Preferred polymers of formulae (V) and (V-1) to (V-10) may be those of formula (VI)
- Preferred endcap groups R e and R f are H, C1-60 alkyl, or optionally substituted Ce-n aryl or C2-1 0 heteroaryl. More preferred endcap groups R e and R f are H, alkyl having from 1 to 50 carbon atoms or phenyl. Even more preferred endcap groups R e and R f are H, alkyl having from 1 to 40 carbon atoms or phenyl. Still even more preferred endcap groups R e and R f are H, alkyl having from 1 to 30 or from 1 to 20 carbon atoms or phenyl. Most preferred endcap groups R e and R f are H, alkyl having from 1 to 10 carbon atoms or phenyl.
- - M w is at least 5,000, preferably at least 8,000, more preferably at least 10,000;
- R 1 and R 2 are phenyl which is mono- or polysubstituted, preferably mono- substituted in the 4-position (i.e. the para-position), with substituents selected from linear or branched alkyl having from 1 to 60, preferably from 1 to 50, more preferably from 1 to 40, even more preferably from 1 to 30 and most preferably from 1 to 20 carbon atoms, wherein one or more H may optionally be replaced by F;
- R S may be selected independently at each occurrence from the group consisting of primary alkyl having from 1 to 60, preferably from 1 to 50, more preferably from 1 to 40 and most preferably from 1 to 30 carbon atoms, secondary alkyl having from 3 to 60, preferably from 1 to 50, more preferably from 1 to 40 and most preferably from 1 to 30 carbon atoms, and tertiary alkyl having from 4 to 60, preferably from 1 to 50, more preferably from 1 to 40 and most preferably from 1 to 30 carbon atoms, wherein one or more H may optionally be replaced by F;
- R s may be selected independently at each occurrence from the group consisting of aryl and heteroaryl, each of which may optionally be fluorinated, alkylated or alkoxylated and has from 4 to 30 ring atoms; R s is selected, on each occurrence identically or differently, from the group consisting of aryl and heteroaryl, each of which is optionally fluorinated, or alkylated and has 4 to 30 ring atoms,
- R s is selected, on each occurrence identically or differently, from the group consisting of primary alkoxy or sulfanylalkyl with 1 to 60, preferably from 1 to 50, more preferably from 1 to 40 and most preferably from 1 to 30 C atoms, secondary alkoxy or sulfanylalkyl with 3 to 60, preferably from 1 to 50, more preferably from 1 to 40 and most preferably from 1 to 30 C atoms, and tertiary alkoxy or sulfanylalkyl with 4 to 60, preferably from 1 to 50, more preferably from 1 to 40 and most preferably from 1 to 30 C atoms, wherein in all these groups one or more H atoms are optionally replaced by F,
- R s is selected, on each occurrence identically or differently, from the group consisting of aryloxy and heteroaryloxy, each of which is optionally alkylated or alkoxylated and has 4 to 30 ring atoms,
- R s is selected,on each occurrence identically or differently, from the group consisting of alkylcarbonyl, alkoxycarbonyl and alkylcarbonyloxy, all of which are straight-chain or branched, are optionally fluorinated, and have from 1 to 60, preferably from 1 to 50, more preferably from 1 to 40 and most preferably from 1 to 30 C atoms,
- R° and R 00 are selected from H or Ci-C 6 o-alkyl, preferably from H or C1-C50- alkyl, more preferably from H or Ci-C4o-alkyl, even preferably from H or Q- C 3 o-alkyl, still even preferably from H or Ci-C2o-alkyl and most preferably from H or Ci-Cio-alkyl,
- the compounds of the present invention can be synthesized according to or in analogy to methods that are known to the skilled person and are described in the literature. Other methods of preparation can be taken from the examples.
- the polymers can be suitably prepared by aryl-aryl coupling reactions, such as Yamamoto coupling, Suzuki coupling, Stille coupling, Sonogashira coupling, Heck coupling or Buchwald coupling. Suzuki coupling, Stille coupling and Yamamoto coupling are especially preferred.
- the monomers which are polymerized to form the repeat units of the polymers can be prepared according to methods which are known to the person skilled in the art.
- the polymers are prepared from monomers of general formula (Il-b) or their preferred subformulae as described above and below.
- Another aspect of the invention is a process for preparing a polymer by coupling one or more identical or different monomelic units comprising said fused-ring moiety or monomers of general formula (Il-a) with each other and/or with one or more co- monomers in a polymerisation reaction, preferably in an aryl-aryl, aryl-alkenyl, or aryl-alkynyl coupling reaction.
- Suitable and preferred comonomers may be selected from the following formulae
- Ar a , Ar b , Ar d m2, m4, R° and R d are as defined herein.
- Very preferred is a process for preparing a polymer by coupling one or more monomers selected from formula (III-a-1) or (III-a-2) with one or more monomers of formula (VII-1), and optionally with one or more monomers selected from formula (VII-2) and (VII-3), in an aryl-aryl coupling reaction, wherein preferably R° and R d are selected from CI, Br, I, -B(OZ 2 ) 2 and -Sn(Z 4 ) 3 .
- preferred embodiments of the present invention relate to a)a process of preparing a polymer by coupling a monomer of formula (VII-1)
- R c -Ar d -R d (VII-3) in an aryl-aryl coupling reaction wherein Ar a , Ar b , Ar d , U a , U b , R c and R d are as defined herein, with R c and R d preferably selected from CI, Br, I, -B(OZ 2 ) 2 and -Sn(Z 4 ) 3 as defined in respect to formulae (Il-a) and (Il-b).
- aryl-aryl coupling and polymerisation methods used in the processes described above and below are Yamamoto coupling, Kumada coupling, Negishi coupling, Suzuki coupling, Stille coupling, Sonogashira coupling, Heck coupling, C- H activation coupling, Ullmann coupling or Buchwald coupling.
- Yamamoto coupling is described for example in WO 00/53656 Al.
- Negishi coupling is described for example in J. Chem. Soc, Chem. Commun., 1977, 683-684.
- Yamamoto coupling is described for example in T. Yamamoto et al., Prog. Polym.
- Stille coupling is described for example in Z. Bao et al., J. Am. Chem. Soc, 1995, 117, 12426-12435.
- monomers having two reactive halide groups are preferably used.
- Suzuki coupling compounds of formula (IV-b) having two reactive boronic acid or boronic acid ester groups or two reactive halide groups are preferably used.
- Stille coupling monomers having two reactive stannane groups or two reactive halide groups are preferably used.
- Negishi coupling monomers having two reactive organozinc groups or two reactive halide groups are preferably used.
- Preferred catalysts are selected from Pd(0) complexes or Pd(II) salts.
- Preferred Pd(0) complexes are those bearing at least one phosphine ligand, for example Pd(Ph 3 P) 4 .
- Another preferred phosphine ligand is tris(or/ 2o-tolyl)phosphine, for example Pd(o-Tol 3 P) 4 .
- Preferred Pd(II) salts include palladium acetate, for example Pd(OAc) 2 .
- the Pd(0) complex can be prepared by mixing a Pd(0) dibenzylideneacetone complex, for example tris(dibenzyl-ideneacetone)dipalladium(0), bis(dibenzylideneacetone)-palladium(0), or Pd(II) salts e.g. palladium acetate, with a phosphine ligand, for example triphenylphosphine, tris(or/ 2o-tolyl)phosphine or tri(tert-butyl)phosphine.
- a Pd(0) dibenzylideneacetone complex for example tris(dibenzyl-ideneacetone)dipalladium(0), bis(dibenzylideneacetone)-palladium(0), or Pd(II) salts e.g. palladium acetate
- a phosphine ligand for example triphenylphosphine, tris(or/ 2o-tolyl)pho
- Suzuki polymerisation is performed in the presence of a base, for example sodium carbonate, potassium carbonate, lithium hydroxide, potassium phosphate or an organic base such as tetraethylammonium carbonate or tetraethylammonium hydroxide.
- a base for example sodium carbonate, potassium carbonate, lithium hydroxide, potassium phosphate or an organic base such as tetraethylammonium carbonate or tetraethylammonium hydroxide.
- Yamamoto polymerisation employs a Ni(0) complex, for example bis(l,5- cyclooctadienyl)nickel(O).
- Suzuki and Stille polymerisation may be used to prepare homopolymers as well as statistical, alternating and block random copolymers.
- Statistical or block copolymers can be prepared for example from the above monomers of formula (VI) or its subformulae, wherein one of the reactive groups is halogen and the other reactive group is a boronic acid, boronic acid derivative group or and alkylstannane.
- the synthesis of statistical, alternating and block copolymers is described in detail for example in WO 03/048225 A2 or WO 2005/014688 A2.
- leaving groups of formula -O-SO 2 Z 1 can be used wherein Z 1 is as described above.
- Particular examples of such leaving groups are tosylate, mesylate and triflate.
- the compounds and polymers according to the present invention can also be used in mixtures or polymer blends, for example together with small molecules or monomeric compounds or together with other polymers having charge-transport, semiconducting, electrically conducting, photoconducting and/or light emitting semiconducting properties, or for example with polymers having hole blocking or electron blocking properties for use as interlayers or charge blocking layers in OLED devices.
- another aspect of the invention relates to a polymer blend comprising one or more polymers according to the present invention and one or more further polymers having one or more of the above-mentioned properties. These blends can be prepared by conventional methods that are described in the prior art and are known to the skilled person. Typically the polymers are mixed with each other or dissolved in suitable solvents and the solutions combined.
- Another aspect of the invention relates to a formulation comprising one or more small molecules, polymers, mixtures or polymer blends as described above and below and one or more organic solvents.
- Preferred solvents are aliphatic hydrocarbons, chlorinated hydrocarbons, aromatic hydrocarbons, ketones, ethers and mixtures thereof. Additional solvents which can be used include 1,2,4-trimethylbenzene, 1,2,3,4-tetra-methyl benzene, pentylbenzene, mesitylene, cumene, cymene, cyclohexylbenzene, diethylbenzene, tetralin, decalin, 2,6-lutidine, 2-fluoro-m-xylene, 3-fluoro-o-xylene, 2-chlorobenzotrifluoride, N,N- dimethylformamide, 2-chloro-6-fluorotoluene, 2-fluoroanisole, anisole, 2,3- dimethylpyrazine, 4-fluoroanisole, 3-fluoroanisole, 3-trifluoro-methylanisole, 2- methylanisole, phenetol, 4-methylanisole, 3-methylanisole, 4-fluor
- solvents include, without limitation, dichloromethane, trichloromethane, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4- dioxane, acetone, methylethylketone, 1 ,2-dichloroethane, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, n-butyl acetate, N,N-dimethylformamide, dimethylacetamide, dimethylsulfoxide, tetraline, decaline, indane, methyl benzoate, ethyl benzoate, mesitylene and/or mixtures thereof.
- the concentration of the compounds or polymers in the solution is preferably 0.1 to 10% by weight, more preferably 0.5 to 5% by weight, with % by weight given relative to the total weight of the solution.
- the solution also comprises one or more binders to adjust the rheological properties, as described for example in WO 2005/055248 Al.
- solutions are evaluated as one of the following categories: complete solution, borderline solution or insoluble.
- the contour line is drawn to outline the solubility parameter-hydrogen bonding limits dividing solubility and insolubility.
- Solvent blends may also be used and can be identified as described in Solvents, W.H. Ellis, Federation of Societies for Coatings Technology, p. 9-10, 1986. Such a procedure may lead to a blend of 'non' -solvents that will dissolve both the polymers of the present invention, although it is desirable to have at least one true solvent in a blend.
- the compounds and polymers according to the present invention can also be used in patterned OSC layers in the devices as described above and below. For applications in modern microelectronics it is generally desirable to generate small structures or patterns to reduce cost (more devices/unit area), and power consumption. Patterning of thin layers comprising a polymer according to the present invention can be carried out for example by photolithography, electron beam lithography or laser patterning.
- the compounds, polymers, polymer blends or formulations of the present invention may be deposited by any suitable method.
- Liquid coating of devices is more desirable than vacuum deposition techniques.
- Solution deposition methods are especially preferred.
- the formulations of the present invention enable the use of a number of liquid coating techniques.
- Preferred deposition techniques include, without limitation, dip coating, spin coating, ink jet printing, nozzle printing, letter-press printing, screen printing, gravure printing, doctor blade coating, roller printing, reverse-roller printing, offset lithography printing, dry offset lithography printing, flexographic printing, web printing, spray coating, curtain coating, brush coating, slot dye coating or pad printing.
- Inkjet printing is particularly preferred when high resolution layers and devices need to be prepared.
- Selected formulations of the present invention may be applied to prefabricated device substrates by ink jet printing or microdispensing.
- industrial piezoelectric print heads such as but not limited to those supplied by Aprion, Hitachi-Koki, InkJet Technology, On Target Technology, Picojet, Spectra, Trident, Xaar may be used to apply the organic semiconductor layer to a substrate.
- semi-industrial heads such as those manufactured by Brother, Epson, Konica, Seiko Instruments Toshiba TEC or single nozzle microdispensers such as those produced by Microdrop and Microfab may be used.
- solvents must fulfill the requirements stated above and must not have any detrimental effect on the chosen print head. Additionally, solvents should have boiling points >100°C, preferably >140°C and more preferably >150°C in order to prevent operability problems caused by the solution drying out inside the print head.
- suitable solvents include substituted and non-substituted xylene derivatives, di-Ci-2-alkyl formamide, substituted and non-substituted anisoles and other phenol- ether derivatives, substituted heterocycles such as substituted pyridines, pyrazines, pyrimidines, pyrrolidinones, substituted and non-substituted N,N-di-Ci-2-alkylanilines and other fluorinated or chlorinated aromatics.
- a preferred solvent for depositing a compound or polymer according to the present invention by ink jet printing comprises a benzene derivative which has a benzene ring substituted by one or more substituents wherein the total number of carbon atoms among the one or more substituents is at least three.
- the benzene derivative may be substituted with a propyl group or three methyl groups, in either case there being at least three carbon atoms in total.
- Such a solvent enables an ink jet fluid to be formed comprising the solvent with the compound or polymer, which reduces or prevents clogging of the jets and separation of the components during spraying.
- the solvent(s) may include those selected from the following list of examples: dodecylbenzene, l-methyl-4-tert-butylbenzene, terpineol, limonene, isodurene, terpinolene, cymene, diethylbenzene.
- the solvent may be a solvent mixture, that is a combination of two or more solvents, each solvent preferably having a boiling point >100°C, more preferably >140°C. Such solvent(s) also enhance film formation in the layer deposited and reduce defects in the layer.
- the ink jet fluid (that is mixture of solvent, binder and semiconducting compound) preferably has a viscosity at 20°C of 1-100 mPa-s, more preferably 1-50 mPa-s and most preferably 1-30 mPa s.
- the polymer blends and formulations according to the present invention can additionally comprise one or more further components or additives selected for example from surface-active compounds, lubricating agents, wetting agents, dispersing agents, hydrophobing agents, adhesive agents, flow improvers, defoaming agents, deaerators, diluents which may be reactive or non-reactive, auxiliaries, colourants, dyes or pigments, sensitizers, stabilizers, nanoparticles or inhibitors.
- the compounds and polymers to the present invention are useful as charge transport, semiconducting, electrically conducting, photoconducting or light emitting materials in optical, electrooptical, electronic, electroluminescent or photoluminescent components or devices.
- the polymers of the present invention are typically applied as thin layers or films.
- the present invention also provides the use of the semiconducting compound, polymer, polymers blend, formulation or layer in an electronic device.
- the formulation may be used as a high mobility semiconducting material in various devices and apparatus.
- the formulation may be used, for example, in the form of a semiconducting layer or film.
- the present invention provides a semiconducting layer for use in an electronic device, the layer comprising a compound, polymer blend or formulation according to the invention.
- the layer or film may be less than about 30 microns.
- the thickness may be less than about 1 micron thick.
- the layer may be deposited, for example on a part of an electronic device, by any of the aforementioned solution coating or printing techniques.
- the invention additionally provides an electronic device comprising a compound, polymer, polymer blend, formulation or organic semiconducting layer according to the present invention.
- Preferred devices are OFETs, TFTs, ICs, logic circuits, capacitors, RFID tags, OLEDs, OLETs, OPEDs, OPVs, OPDs, solar cells, laser diodes, photoconductors, photodetectors, electrophotographic devices, electrophotographic recording devices, organic memory devices, sensor devices, charge injection layers, Schottky diodes, planarising layers, antistatic films, conducting substrates and conducting patterns.
- Particularly preferred devices are OLEDs.
- Especially preferred electronic device are OFETs, OLEDs, OPV and OPD devices, in particular bulk heterojunction (BHJ) OPV devices.
- the active semiconductor channel between the drain and source may comprise the layer of the invention.
- the charge (hole or electron) injection or transport layer may comprise the layer of the invention.
- the polymer according to the present invention is preferably used in a formulation that comprises or contains, more preferably consists essentially of, very preferably exclusively of, a p-type (electron donor) semiconductor and an n-type (electron acceptor) semiconductor.
- the n-type semiconductor is constituted by a polymer according to the present invention.
- the polymer according to the present invention is blended with a p-type semiconductor, to form the active layer in an OPV or OPD device.
- the device preferably further comprises a first transparent or semi-transparent electrode on a transparent or semi-transparent substrate on one side of the active layer, and a second metallic or semi-transparent electrode on the other side of the active layer.
- the OPV or OPD device comprises, between the active layer and the first or second electrode, one or more additional buffer layers acting as hole transporting layer and/or electron blocking layer, which comprise a material such as metal oxide, like for example, ZTO, MoO x , NiO x , a conjugated polymer electrolyte, like for example PEDOT:PSS, a conjugated polymer, like for example polytriarylamine (PTAA), an organic compound, like for example N,N'-diphenyl-N,N'-bis(l- naphthyl)(l,l'-biphenyl)-4,4'di
- the compounds, polymers, polymer blends or formulations of the present invention may be deposited by any suitable method.
- Liquid coating of devices is more desirable than vacuum deposition techniques.
- Solution deposition methods are especially preferred.
- the formulations of the present invention enable the use of a number of liquid coating techniques.
- Preferred deposition techniques include, without limitation, dip coating, spin coating, ink jet printing, nozzle printing, letter-press printing, screen printing, gravure printing, doctor blade coating, roller printing, reverse-roller printing, offset lithography printing, dry offset lithography printing, flexographic printing, web printing, spray coating, curtain coating, brush coating, slot dye coating or pad printing.
- area printing method compatible with flexible substrates are preferred, for example slot dye coating, spray coating and the like.
- suitable solvent In the preparation of formulations, suitable solvent must be selected to ensure full dissolution of both component, p-type and n-type and take into account the boundary conditions (for example rheological properties) introduced by the chosen printing method.
- Organic solvent are generally used for this purpose.
- Typical solvents can be aromatic solvents, halogenated solvents or chlorinated solvents, including chlorinated aromatic solvents. Examples include, but are not limited to chlorobenzene, 1,2- dichlorobenzene, chloroform, 1,2-dichloroethane, dichloromethane, carbon tetrachloride, toluene, cyclohexanone, ethylacetate, tetrahydrofuran, anisole, morpholine, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methylethylketone, 1,2-dichloroethane, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, n-butyl acetate, dimethylformamide, dimethylacetamide, dimethylsulfoxide, tetraline
- OPV or OPD devices that comprise or contain, more preferably consists essentially of, very preferably exclusively of, a p-type (electron donor) semiconductor and an n-type (electron acceptor) semiconductor, whereas the n-type semiconductor is constituted by a polymer according to the present invention.
- the p-type semiconductor in the said OPV or OPD devices can be an organic or inorganic material.
- the p-type organic semiconductor material used in the said OPV or OPD devices can be either small molecules or oligomers such as for example copper phthalocyanine, zinc phthalocyanine, pentacene, sexithiophenes, and any other p-type small molecule or oligomeric semiconductor (see e.g.
- the p-type inorganic semiconductor material use in the said OPV or OPD devices can be p-type silicon, copper(I) sulfide (CU2S), copper(I) oxide (CU2O), cooper(II) oxide (CuO), copper indium gallium selenide (CIGS), and any other suitable inorganic semiconductor.
- the solvents and formulation procedures that are suitable for processing OPV or OPD devices described above can also be used for the n-type semiconductor that is constituted by a polymer according to the present invention.
- the OPV device can for example be of any type known from the literature (see e.g. Waldauf et ah, Appl. Phys. Lett., 2006, 89, 233517) including very preferably an OPV device where the photoactive layer comprises a p-type polymer semiconductor and an n-type polymer semiconductor (see e.g. Halls, J. J. et al. Nature, 1995, 376, 498-500), where the n-type polymer semiconductor is constituted by a polymer according to the present invention.
- a first preferred OPV device comprises the following layers (in the sequence from bottom to top):
- a high work function electrode preferably comprising a metal oxide, like for example ITO, serving as anode
- an optional conducting polymer layer or hole transport layer preferably comprising an organic poymer or polymer blend, for example of PEDOT:PSS (poly(3,4-ethylenedioxythiophene): poly(styrene-sulfonate), or TBD ( ⁇ , ⁇ '- dyphenyl-N-N'-bis(3-methylphenyl)-l,l 'biphenyl-4,4'-diamine) or NBD (N,N'-dyphenyl-N-N'-bis(l-napthylphenyl)-l, biphenyl-4,4'-diamine), - a layer, also referred to as "active layer", comprising a p-type and an n-type organic semiconductor, which can exist for example as a p-type/n-type bilayer or as distinct p-type and n-type layers, or as blend or p-type and n-type semiconductor, forming a BHJ,
- a layer having electron transport properties for example comprising
- a low work function electrode preferably comprising a metal like for example aluminum, serving as cathode
- At least one of the electrodes preferably the anode, is transparent to visible light
- n-type semiconductor is a polymer according to the present invention.
- a second preferred OPV device is an inverted OPV device and comprises the following layers (in the sequence from bottom to top):
- a high work function metal or metal oxide electrode comprising for example ITO, serving as cathode
- a layer having hole blocking properties preferably comprising a metal oxide like TiO x or Zn x ,
- an active layer comprising a p-type and an n-type organic semiconductor, situated between the electrodes, which can exist for example as a p-type/n-type bilayer or as distinct p-type and n-type layers, or as blend or p-type and n-type semiconductor, forming a BHJ,
- an optional conducting polymer layer or hole transport layer preferably comprising an organic poymer or polymer blend, for example of PEDOT:PSS or TBD or BD,
- an electrode comprising a high work function metal like for example silver, serving as anode
- At least one of the electrodes preferably the cathode, is transparent to visible light
- the n-type semiconductor is a polymer according to the present invention.
- the active layer When the active layer is deposited on the substrate, it forms a BHJ that phase separates at nanoscale level.
- nanoscale phase separation see Dennler et al, Proceedings of the IEEE, 2005, 93 (8), 1429 or Hoppe et al, Adv. Func. Mater, 2004, 14(10), 1005.
- An optional annealing step may be then necessary to optimize blend morpohology and consequently OPV device performance.
- Another method to optimize device performance is to prepare formulations for the fabrication of OPV(BHJ) devices that may include high boiling point additives to promote phase separation in the right way.
- 1,8-Octanedithiol, 1,8-diiodooctane, nitrobenzene, chloronaphthalene, and other additives have been used to obtain high- efficiency solar cells. Examples are disclosed in J. Peet, et al, Nat. Mater., 2007, 6, 497 or Frechet et al. J. Am. Chem. Soc, 2010, 132, 7595-7597.
- the compounds, polymers, formulations and layers of the present invention are also suitable for use in an OFET as the semiconducting channel. Accordingly, the invention also provides an OFET comprising a gate electrode, an insulating (or gate insulator) layer, a source electrode, a drain electrode and an organic semiconducting channel connecting the source and drain electrodes, wherein the organic semiconducting channel comprises a compound, polymer, polymer blend, formulation or organic semiconducting layer according to the present invention.
- an OFET comprising a gate electrode, an insulating (or gate insulator) layer, a source electrode, a drain electrode and an organic semiconducting channel connecting the source and drain electrodes, wherein the organic semiconducting channel comprises a compound, polymer, polymer blend, formulation or organic semiconducting layer according to the present invention.
- Other features of the OFET are well known to those skilled in the art.
- OFETs where an OSC material is arranged as a thin film between a gate dielectric and a drain and a source electrode are generally known, and are described for example in US 5,892,244, US 5,998,804, US 6,723,394 and in the references cited in the background section. Due to the advantages, like low cost production using the solubility properties of the compounds according to the invention and thus the processibility of large surfaces, preferred applications of these FETs are such as integrated circuitry, TFT displays and security applications.
- the gate, source and drain electrodes and the insulating and semiconducting layer in the OFET device may be arranged in any sequence, provided that the source and drain electrode are separated from the gate electrode by the insulating layer, the gate electrode and the semiconductor layer both contact the insulating layer, and the source electrode and the drain electrode both contact the semiconducting layer.
- An OFET device according to the present invention preferably comprises:
- the semiconductor layer preferably comprises a compound, polymer, polymer blend or formulation as described above and below.
- the OFET device can be a top gate device or a bottom gate device. Suitable structures and manufacturing methods of an OFET device are known to the skilled in the art and are described in the literature, for example in US 2007/0102696 Al.
- the gate insulator layer preferably comprises a fluoropolymer, like e.g. the commercially available Cytop 809M® or Cytop 107M® (from Asahi Glass).
- a fluoropolymer like e.g. the commercially available Cytop 809M® or Cytop 107M® (from Asahi Glass).
- the gate insulator layer is deposited, e.g. by spin-coating, doctor blading, wire bar coating, spray or dip coating or other known methods, from a formulation comprising an insulator material and one or more solvents with one or more fluoro atoms (fluorosolvents), preferably a perfluorosolvent.
- fluorosolvents fluoro atoms
- a suitable perfluorosolvent is e.g. FC75® (available from Acros, catalogue number 12380).
- fluoropolymers and fluorosolvents are known in prior art, like for example the perfluoropolymers Teflon AF® 1600 or 2400 (from DuPont) or Fluoropel® (from Cytonix) or the perfluorosolvent FC 43® (Acros, No. 12377).
- OFETs and other devices with semiconducting materials according to the present invention can be used for RFID tags or security markings to authenticate and prevent counterfeiting of documents of value like banknotes, credit cards or ID cards, national ID documents, licenses or any product with monetary value, like stamps, tickets, shares, cheques etc.
- the materials according to the invention can be used in OLEDs, e.g. as the active display material in a flat panel display applications, or as backlight of a flat panel display like e.g. a liquid crystal display.
- OLEDs are realized using multilayer structures.
- An emission layer is generally sandwiched between one or more electron-transport and/or hole-transport layers.
- the inventive compounds, materials and films may be employed in one or more of the charge transport layers and/or in the emission layer, corresponding to their electrical and/or optical properties.
- the compounds, materials and films according to the invention show electroluminescent properties themselves or comprise electroluminescent groups or compounds.
- the selection, characterization as well as the processing of suitable monomeric, oligomeric and polymeric compounds or materials for the use in OLEDs is generally known by a person skilled in the art, see, e.g., Miiller et al, Synth. Metals, 2000, 111-112, 31-34, Alcala, J. Appl. Phys., 2000, 88, 7124-7128 and the literature cited therein.
- the materials according to this invention especially those showing photoluminescent properties, may be employed as materials of light sources, e.g.
- a further aspect of the invention relates to both the oxidised and reduced form of the compounds according to this invention. Either loss or gain of electrons results in formation of a highly delocalised ionic form, which is of high conductivity. This can occur on exposure to common dopants. Suitable dopants and methods of doping are known to those skilled in the art, e.g. from EP 0 528 662, US 5,198,153 or WO 96/21659.
- the doping process typically implies treatment of the semiconductor material with an oxidating or reducing agent in a redox reaction to form delocalised ionic centres in the material, with the corresponding counterions derived from the applied dopants.
- Suitable doping methods comprise for example exposure to a doping vapor in the atmospheric pressure or at a reduced pressure, electrochemical doping in a solution containing a dopant, bringing a dopant into contact with the semiconductor material to be thermally diffused, and ion-implantation of the dopant into the semiconductor material.
- suitable dopants are for example halogens (e.g., , Cl 2 , Br 2 , IC1, IC1 3 , IBr and IF), Lewis acids (e.g., PF 5 , AsF 5 , SbF 5 , BF 3 , BC1 3 , SbCl5, BBr 3 and S0 3 ), protonic acids, organic acids, or amino acids (e.g., HF, HC1, HN0 3 , H 2 S0 4 , HCIO 4 , FS0 3 H and C1S0 3 H), transition metal compounds (e.g., FeCl 3 , FeOCl, Fe(C10 4 ) 3 , Fe(4-CH 3 C 6 H 4 S0 3 ) 3 , TiCl 4 , ZrCl 4 , HfCl 4 , NbF 5 , NbCl 5 , Tads, M0F 5 , M0CI 5 , WF 5 ,
- halogens
- examples of dopants are cations (e.g., H + , Li + , Na + , K + , Rb + and Cs + ), alkali metals (e.g., Li, Na, K, Rb, and Cs), alkaline-earth metals (e.g., Ca, Sr, and Ba), 0 2 , XeOF 4 , ( 0 2 + ) (SbF 6 ), (N0 2 + ) (SbCl 6 ), ( 0 2 + ) (BF 4 ), AgC10 4 , H 2 IrCl 6 , La(N0 3 ) 3 6H 2 0, FS0 2 OOS0 2 F, europium acetylcholine, R 4 N + , (R is an alkyl group), ⁇ ⁇ + (R is an alkyl group), ReAs + (R is an alkyl group), and R 3 S + (R is an alkyl group).
- dopants are cations (
- the conducting form of the compounds of the present invention can be used as an organic "metal" in applications including, but not limited to, charge injection layers and ITO planarising layers in OLED applications, films for flat panel displays and touch screens, antistatic films, printed conductive substrates, patterns or tracts in electronic applications such as printed circuit boards and condensers.
- the compounds and formulations according to the present invention may also be suitable for use in organic plasmon-emitting diodes (OPEDs), as described for example in Koller et ah, Nat. Photonics, 2008, 2, 684.
- OPEDs organic plasmon-emitting diodes
- the materials according to the present invention can be used alone or together with other materials in or as alignment layers in LCD or OLED devices, as described for example in US 2003/0021913.
- the use of charge transport compounds according to the present invention can increase the electrical conductivity of the alignment layer.
- this increased electrical conductivity can reduce adverse residual dc effects in the switchable LCD cell and suppress image sticking or, for example in ferroelectric LCDs, reduce the residual charge produced by the switching of the spontaneous polarisation charge of the ferroelectric LCs.
- this increased electrical conductivity can enhance the electroluminescence of the light emitting material.
- the compounds or materials according to the present invention having mesogenic or liquid crystalline properties can form oriented anisotropic films as described above, which are especially useful as alignment layers to induce or enhance alignment in a liquid crystal medium provided onto said anisotropic film.
- the materials according to the present invention may also be combined with photoisomerisable compounds and/or chromophores for use in or as photoalignment layers, as described in US 2003/0021913 Al.
- the materials according to the present invention can be employed as chemical sensors or materials for detecting and discriminating DNA sequences.
- Such uses are described for example in L. Chen, D. W. McBranch, H. Wang, R. Helgeson, F. Wudl and D. G. Whitten, Proc. Natl. Acad. Sci. U.S.A., 1999, 96, 12287; D. Wang, X. Gong, P. S. Heeger, F. Rininsland, G. C. Bazan and A. J. Heeger, Proc. Natl. Acad. Sci.
- the solid was then purified through column chromatography on silica gel using dichloromethane : hexane (1 :1, v:v) as the eluent to yield a dark purple solid (1.6 g).
- the solid was recrystallized from isopropanol to give the target product. Yield: 1.33 g (69.0 %).
- 6-bromo-l-(4-octadecyldocosyl)indoline-2,3-dione (0.420 g, 0.534 mmol)
- benzo[l,2- 4,5-Z ]difuran-2,6(3H,7H)-dione 0.051 g, 0.267 mmol
- p-TsOH p-toluenesulfonic acid
- a bottom-contact, bottom-gate OTFT configuration was used.
- Heavily p-doped Si wafer functions as the gate electrode and a thermally grown S1O 2 layer ( ⁇ 200 nm)
- DTS dodecyltrichlorosilane
- a polymer solution in chloroform (10 mg/ cm 3 ) was spin coated on the substrate at 3000 rpm for 60 seconds to give a film, which was subject to thermal annealing at different temperature for 15 minutes in a glove box.
- OTFT devices have a channel length (L) of 30 ⁇ and a channel width (W) of 1000 ⁇ .
- the devices were characterized in air using an Agilent 4155C Semiconductor Analyzer.
- the carrier mobilit in the saturated regime, ⁇ 8 ⁇ was calculated according to the equation of , where I DS is the drain current, C, is the capacitance per unit area of the gate dielectric, W and L are, respectively, the semiconductor channel width and length, and VG and VT are, respectively, the gate voltage and threshold voltage. VT of the devices was determine from extrapolation of
- OTFT characteristics of the exemplary polymers are summarized in Table 1 for electron enhancement mode and in Table 2 for hole enhancement mode, with ⁇ 6 denoting the electron mobility, ⁇ 3 ⁇ 4 denoting the hole mobility, and WW denoting the current on-to-off ratio.
- Output and transfer curves of typical devices using the exemplary polymers are shown in Figure 5 through Figure 10.
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Abstract
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
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Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
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Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1251082A (en) * | 1967-09-13 | 1971-10-27 | ||
DE3618838A1 (en) * | 1985-06-11 | 1986-12-11 | Basf Ag, 67063 Ludwigshafen | Copolycondensates of the polyindophenine type |
WO2001032577A1 (en) * | 1999-11-03 | 2001-05-10 | Ciba Specialty Chemicals Holding Inc. | Pigmented vitreous material its precursor glass items coated therewith and method of its preparation |
US6492533B1 (en) * | 2001-09-18 | 2002-12-10 | Milliken & Company | Bismethine benzodifuranone derivative colorants |
US20060223993A1 (en) * | 2005-04-01 | 2006-10-05 | Connor Daniel M | Colorant compounds, intermediates, and compositions |
WO2009010521A2 (en) * | 2007-07-19 | 2009-01-22 | Basf Se | Nir-inert substrates comprising bis-oxodihydroindolylen-benzodifuranones |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5789298B2 (en) * | 2010-07-09 | 2015-10-07 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングMerck Patent Gesellschaft mit beschraenkter Haftung | Semiconducting polymer |
US9217070B2 (en) * | 2012-06-01 | 2015-12-22 | Basf Se | Black colorant mixture |
-
2013
- 2013-11-07 JP JP2015540974A patent/JP2016505516A/en active Pending
- 2013-11-07 WO PCT/CA2013/050854 patent/WO2014071524A1/en active Application Filing
- 2013-11-07 US US14/441,614 patent/US20150295179A1/en not_active Abandoned
- 2013-11-07 CN CN201380058188.9A patent/CN104812795A/en active Pending
- 2013-11-07 EP EP13853712.1A patent/EP2917261A4/en not_active Withdrawn
- 2013-11-07 KR KR1020157015000A patent/KR20150082540A/en not_active Application Discontinuation
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1251082A (en) * | 1967-09-13 | 1971-10-27 | ||
DE3618838A1 (en) * | 1985-06-11 | 1986-12-11 | Basf Ag, 67063 Ludwigshafen | Copolycondensates of the polyindophenine type |
WO2001032577A1 (en) * | 1999-11-03 | 2001-05-10 | Ciba Specialty Chemicals Holding Inc. | Pigmented vitreous material its precursor glass items coated therewith and method of its preparation |
US6492533B1 (en) * | 2001-09-18 | 2002-12-10 | Milliken & Company | Bismethine benzodifuranone derivative colorants |
US20060223993A1 (en) * | 2005-04-01 | 2006-10-05 | Connor Daniel M | Colorant compounds, intermediates, and compositions |
WO2009010521A2 (en) * | 2007-07-19 | 2009-01-22 | Basf Se | Nir-inert substrates comprising bis-oxodihydroindolylen-benzodifuranones |
Non-Patent Citations (3)
Title |
---|
KOSSMEHL G. ET AL.: "Synthese, Charakterisierung und Halbleitereigenschaften eines polymeren Indopheninhomologen", DIE MAKROMOLEKULARE CHEMIE, vol. 176, 1975, pages 333 - 340, XP055253369 * |
LI Y. ET AL.: "Design of high mobility DPP-based polymer semiconductors for organic thin film transistors", POLYMER PREPRINTS, vol. 52, no. 2, 2001, pages 941 - 942, XP008179172 * |
See also references of EP2917261A4 * |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
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CN104045819A (en) * | 2014-05-21 | 2014-09-17 | 合肥工业大学 | Ultralow-band gap donor-receptor conjugated polymer and preparation method thereof |
WO2017148864A1 (en) | 2016-02-29 | 2017-09-08 | Basf Se | Semiconducting polymer |
US10815236B2 (en) | 2016-02-29 | 2020-10-27 | Basf Se | Semiconducting polymer |
TWI717468B (en) * | 2016-02-29 | 2021-02-01 | 南韓商Clap股份有限公司 | Semiconducting polymer |
CN108699073B (en) * | 2016-02-29 | 2021-08-17 | Clap有限公司 | Semiconducting polymers |
US11283023B2 (en) | 2017-06-08 | 2022-03-22 | Corning Incorporated | Doping of other polymers into organic semi-conducting polymers |
US11897884B2 (en) | 2017-06-13 | 2024-02-13 | Yeda Research And Development Co. Ltd. | Small molecules based free-standing films and hybrid materials |
WO2022262159A1 (en) | 2021-06-18 | 2022-12-22 | 华南理工大学 | N-type conjugated polymer, preparation method therefor, and application thereof |
Also Published As
Publication number | Publication date |
---|---|
US20150295179A1 (en) | 2015-10-15 |
EP2917261A4 (en) | 2016-11-16 |
KR20150082540A (en) | 2015-07-15 |
EP2917261A1 (en) | 2015-09-16 |
JP2016505516A (en) | 2016-02-25 |
CN104812795A (en) | 2015-07-29 |
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